Jesse Middleton
@jessemiddleton.com
@srcasm on Twitter. Parent to a splendid eight year old son and rambunctious one year old daughter. Husband to a brilliant woman. GP at Flybridge and co-founder of Next Wave NYC and WeWork Labs.
Looking forward to finding somebody amazing to join our small but mighty team here at Flybridge. www.linkedin.com/jobs/view/42...
Flybridge hiring Chief of Staff to a General Partner in New York, NY | LinkedIn
Posted 12:59:22 PM. About FlybridgeFlybridge is the early-stage venture capital firm backing the next wave of our…See this and similar jobs on LinkedIn.
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July 3, 2025 at 3:50 PM
Looking forward to finding somebody amazing to join our small but mighty team here at Flybridge. www.linkedin.com/jobs/view/42...
I'm happy if you want to share a little bit more color about "Why you", but we want to run a good process here, so please apply to the job post below. You can send a more detailed note to jesse+cos@flybridge.com after you've submitted the application.
July 3, 2025 at 3:50 PM
I'm happy if you want to share a little bit more color about "Why you", but we want to run a good process here, so please apply to the job post below. You can send a more detailed note to jesse+cos@flybridge.com after you've submitted the application.
I'm really excited to loop the right person into everything that I'm working on and that our team is doing over the coming years.
If you know somebody who'd be an amazing fit, send them here and ask them to apply over on LinkedIn (link in the next Tweet).
If you know somebody who'd be an amazing fit, send them here and ask them to apply over on LinkedIn (link in the next Tweet).
July 3, 2025 at 3:50 PM
I'm really excited to loop the right person into everything that I'm working on and that our team is doing over the coming years.
If you know somebody who'd be an amazing fit, send them here and ask them to apply over on LinkedIn (link in the next Tweet).
If you know somebody who'd be an amazing fit, send them here and ask them to apply over on LinkedIn (link in the next Tweet).
I want this person to be the "COO" to my CEO brain. You should be:
• Detail-oriented and amazing with people
• Passionate about startups and learning the venture business
• Excited to work with some of the smartest and most driven founders in the world
• Detail-oriented and amazing with people
• Passionate about startups and learning the venture business
• Excited to work with some of the smartest and most driven founders in the world
July 3, 2025 at 3:50 PM
I want this person to be the "COO" to my CEO brain. You should be:
• Detail-oriented and amazing with people
• Passionate about startups and learning the venture business
• Excited to work with some of the smartest and most driven founders in the world
• Detail-oriented and amazing with people
• Passionate about startups and learning the venture business
• Excited to work with some of the smartest and most driven founders in the world
I'm grateful for people who accept me as I am, including Jeff, Chip, and Cat. You teach me more every day.
P.S. Today is also my parents' 43rd wedding anniversary :)
Happy Friday!
P.S. Today is also my parents' 43rd wedding anniversary :)
Happy Friday!
June 13, 2025 at 2:54 PM
I'm grateful for people who accept me as I am, including Jeff, Chip, and Cat. You teach me more every day.
P.S. Today is also my parents' 43rd wedding anniversary :)
Happy Friday!
P.S. Today is also my parents' 43rd wedding anniversary :)
Happy Friday!
I encourage the entrepreneurs I back to prioritize their wellbeing. Startups are challenging enough when you're at your best.
Sobriety has taught me to be fully present. Flybridge has taught me to trust my instincts. Together, that’s a powerful combination.
Sobriety has taught me to be fully present. Flybridge has taught me to trust my instincts. Together, that’s a powerful combination.
June 13, 2025 at 2:54 PM
I encourage the entrepreneurs I back to prioritize their wellbeing. Startups are challenging enough when you're at your best.
Sobriety has taught me to be fully present. Flybridge has taught me to trust my instincts. Together, that’s a powerful combination.
Sobriety has taught me to be fully present. Flybridge has taught me to trust my instincts. Together, that’s a powerful combination.
Instead of micromanaging, they told me: "You'll be here longer than us. Start making the calls." That level of trust changed me.
The experience shaped how I work with founders. While everyone talks about work-life balance, most of us struggle with it.
The experience shaped how I work with founders. While everyone talks about work-life balance, most of us struggle with it.
June 13, 2025 at 2:54 PM
Instead of micromanaging, they told me: "You'll be here longer than us. Start making the calls." That level of trust changed me.
The experience shaped how I work with founders. While everyone talks about work-life balance, most of us struggle with it.
The experience shaped how I work with founders. While everyone talks about work-life balance, most of us struggle with it.
Sobriety taught me that the strongest relationships don't require alcohol.
From my first day at Flybridge, Jeff and Chip demonstrated this. They focus on meaningful work and authentic relationships with founders.
From my first day at Flybridge, Jeff and Chip demonstrated this. They focus on meaningful work and authentic relationships with founders.
June 13, 2025 at 2:54 PM
Sobriety taught me that the strongest relationships don't require alcohol.
From my first day at Flybridge, Jeff and Chip demonstrated this. They focus on meaningful work and authentic relationships with founders.
From my first day at Flybridge, Jeff and Chip demonstrated this. They focus on meaningful work and authentic relationships with founders.
Generic AI contract review is commoditizing fast. Fully-captive workflows are still rare. LP documentation is rule-heavy and repeatable. That’s ideal training data.
May 7, 2025 at 2:29 PM
Generic AI contract review is commoditizing fast. Fully-captive workflows are still rare. LP documentation is rule-heavy and repeatable. That’s ideal training data.
Distribution:
Half of Covenant’s early adopters sit within three subway stops of our office. Jen’s network supplies the first ~20 customers. Product proof handles the next >200.
Half of Covenant’s early adopters sit within three subway stops of our office. Jen’s network supplies the first ~20 customers. Product proof handles the next >200.
May 7, 2025 at 2:29 PM
Distribution:
Half of Covenant’s early adopters sit within three subway stops of our office. Jen’s network supplies the first ~20 customers. Product proof handles the next >200.
Half of Covenant’s early adopters sit within three subway stops of our office. Jen’s network supplies the first ~20 customers. Product proof handles the next >200.
Market size:
The niche legal spend is “only” $5 billion, which keeps platform tourists away. Own 20% and you’re running a billion-dollar ARR business with near-zero churn (LPs rarely switch counsel mid-fund).
The niche legal spend is “only” $5 billion, which keeps platform tourists away. Own 20% and you’re running a billion-dollar ARR business with near-zero churn (LPs rarely switch counsel mid-fund).
May 7, 2025 at 2:29 PM
Market size:
The niche legal spend is “only” $5 billion, which keeps platform tourists away. Own 20% and you’re running a billion-dollar ARR business with near-zero churn (LPs rarely switch counsel mid-fund).
The niche legal spend is “only” $5 billion, which keeps platform tourists away. Own 20% and you’re running a billion-dollar ARR business with near-zero churn (LPs rarely switch counsel mid-fund).
Ingest LP documents → LLM reviews every term → output a signature-ready closing binder.
Why buyers care:
• Speed: hours, not days
• Consistency: once tagged, never missed
• Cost: ~90 % below big-law
Why buyers care:
• Speed: hours, not days
• Consistency: once tagged, never missed
• Cost: ~90 % below big-law
May 7, 2025 at 2:29 PM
Ingest LP documents → LLM reviews every term → output a signature-ready closing binder.
Why buyers care:
• Speed: hours, not days
• Consistency: once tagged, never missed
• Cost: ~90 % below big-law
Why buyers care:
• Speed: hours, not days
• Consistency: once tagged, never missed
• Cost: ~90 % below big-law
Across U.S. institutions, that line item added up to roughly $5 billion last year. Covenant automates that narrow yet stubbornly expensive workflow.
How it works:
How it works:
May 7, 2025 at 2:29 PM
Across U.S. institutions, that line item added up to roughly $5 billion last year. Covenant automates that narrow yet stubbornly expensive workflow.
How it works:
How it works:
I have no idea if they know it or will remember it but it makes me feel like in a crazy world where we have little control, from day to day, there’s this tiny period of time when it’s just us, together, and complete. 💜
May 4, 2025 at 6:19 PM
I have no idea if they know it or will remember it but it makes me feel like in a crazy world where we have little control, from day to day, there’s this tiny period of time when it’s just us, together, and complete. 💜
What a magical idea and execution. Started a small Dad Group in NYC but we’re not cool enough to have merch just yet. 😏 Entrepreneurs, VCs, designers, chefs, and dentists all come together though.
April 14, 2025 at 1:05 AM
What a magical idea and execution. Started a small Dad Group in NYC but we’re not cool enough to have merch just yet. 😏 Entrepreneurs, VCs, designers, chefs, and dentists all come together though.
The main caveat is ensuring that you’re still strategic about where you incorporate or how you handle local regulations. You can’t be sloppy about that.
The world isn’t small, but it’s definitely more connected than ever.
The world isn’t small, but it’s definitely more connected than ever.
March 28, 2025 at 6:58 PM
The main caveat is ensuring that you’re still strategic about where you incorporate or how you handle local regulations. You can’t be sloppy about that.
The world isn’t small, but it’s definitely more connected than ever.
The world isn’t small, but it’s definitely more connected than ever.
Or we see a founder from the Bay Area who flew out to New York just to pitch in front of an AI-focused crowd. It’s a more fluid world. They adapt. We adapt.
March 28, 2025 at 6:58 PM
Or we see a founder from the Bay Area who flew out to New York just to pitch in front of an AI-focused crowd. It’s a more fluid world. They adapt. We adapt.
For me, I like how this expands our investment lens. We can back a company headquartered in New York, but maybe their entire engineering team is in Argentina.
March 28, 2025 at 6:58 PM
For me, I like how this expands our investment lens. We can back a company headquartered in New York, but maybe their entire engineering team is in Argentina.